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Published byNigel Daniel Carter Modified over 9 years ago
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**We will continue talking about acid/base chemistry. Bring the last 5 slides from lecture 6 to lecture 7.**
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Structure and Acidity Hybridization: The greater the % s character of C, the more stable the anion and the more acidic the C-H bond is
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Structure and Acidity Resonance delocalization: the greater the delocalization of negative charge in the anion, the stronger the acid HA is Compare the acidities of ethanol and acid acetic acid, both of which contain an -OH group –ionization of the O-H bond of an alcohol gives an anion for which there is no resonance stabilization
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Structure and Acidity –Ionization of the O-H bond of a carboxylic acid gives a resonance-stabilized anion. Acetate anion is a more stable anion than ethoxide anion and, therefore, acetic acid is a stronger acid than ethanol
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Structure and Acidity Electron-withdrawing inductive effect: withdrawal of electron density from the H-A bond increases the acidity of HA –a carboxylic acid is a stronger acid than an alcohol because of (1) the resonance stabilization of the carboxylate anion and (2) the electron-withdrawing inductive effect of the adjacent carbonyl group
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Position of equilibrium Favors reaction of the stronger acid and stronger base to give the weaker acid and weaker base
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Position of equilibrium Reaction of acetic acid and ammonia
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Position of equilibrium Calculation of K eq –write the equilibrium constant for this acid/base reaction, multiply by [H 3 O + ]/H 3 O + ], rearrange terms, substitute values, and solve
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Position of equilibrium Reaction of acetic acid and sodium bicarbonate
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Lewis Acids and Bases Lewis acid: accepts a pair of electrons to form a new covalent bond Lewis base: donates a pair of electrons to form a new covalent bond
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Lewis Acids and Bases
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